Ethyl 2-[(3-chlorophenyl)hydrazono]-3-oxobutanoate

Abstract

The molecule of the title oxobutanoate derivative, C12H13ClN2O3, adopts a keto–hydrazo tautomeric form and is roughly planar, the angle between the benzene ring and the mean plane through the hydrazone and aliphatic chain being 1.49 (6)°. This planarity is further aided by the formation of an intramolecular N—H...O hydrogen bond which generates anS(6) ring motif. The aromatic ring and aliphatic chain have atransconfiguration with respect to the N—N bond. In the crystal packing, centrosymmetricR22(16) dimers are formed through pairs of weak C—H...O(3-oxo) interactions. These dimers are linked together through weak C—H...O(carboxylate C=O) interactions into ribbons along theb-axis direction. These ribbons are stacked along thea-axis direction. The crystal also exhibits Cl...Cl [3.4988 (6) Å] and C...O [3.167 (2)–3.335 (2) Å] short contacts.